ArticleBioorganic & medicinal chemistry letters2006
Conversion of A3 adenosine receptor agonists into selective antagonists by modification of the 5'-ribofuran-uronamide moiety.
Article in Bioorganic & medicinal chemistry letters, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- 4'-Thionucleosides as adenosine AMedicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2026Review
- Subtle Chemical Changes Cross the Boundary between Agonist and Antagonist: New AJournal of medicinal chemistry · 2021Article
- Design and Synthesis of 2,6-Disubstituted-4'-Selenoadenosine-5'-Pharmaceuticals (Basel, Switzerland) · 2021Article
- Adenosine receptors as promising targets for the management of ocular diseases.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2021Review
- AMedicinal research reviews · 2018Review
- Nucleoside-derived antagonists to A3 adenosine receptors lower mouse intraocular pressure and act across species.Experimental eye research · 2010Article
- Functionalized congeners of A3 adenosine receptor-selective nucleosides containing a bicyclo[3.1.0]hexane ring system.Journal of medicinal chemistry · 2009Article
- Medicinal chemistry of the A3 adenosine receptor: agonists, antagonists, and receptor engineering.Handbook of experimental pharmacology · 2009Review
- Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists.Journal of medicinal chemistry · 2008Article
- Selective A(3) adenosine receptor antagonists derived from nucleosides containing a bicyclo[3.1.0]hexane ring system.Bioorganic & medicinal chemistry · 2008Article
- Translocation of arrestin induced by human A(3) adenosine receptor ligands in an engineered cell line: comparison with G protein-dependent pathways.Pharmacological research · 2008Article
- Structure-activity relationships of 2-chloro-N6-substituted-4'-thioadenosine-5'-N,N-dialkyluronamides as human A3 adenosine receptor antagonists.Bioorganic & medicinal chemistry letters · 2008Article
- Synthesis of 2-chloro-N6-substituted-4'-thioadenosine-5'-N, N-dialkyluronamides as potent and selective A3 adenosine receptor antagonists.Nucleic acids symposium series (2004) · 2008Article
- Design and synthesis of truncated 4'-thioadenosine derivatives as potent and selective A3 adenosine receptor antagonists.Nucleic acids symposium series (2004) · 2008Article
- Design, synthesis, and anti-tumor activity of 4'-thionucleosides as potent and selective agonists at the human A3 adenosine receptor.Nucleosides, nucleotides & nucleic acids · 2007Article
- Stereoselective synthesis of 1'-functionalized-4'-thionucleosides.Nucleosides, nucleotides & nucleic acids · 2007Article
- Docking studies of agonists and antagonists suggest an activation pathway of the A3 adenosine receptor.Journal of molecular graphics & modelling · 2006Article
- Invited Lectures : Overviews Purinergic signalling: past, present and future.Purinergic signalling · 2006Article
- NUCLEOSIDE PRODRUGS OF ACollection of Czechoslovak chemical communications · 2006Article
- Synthesis and Binding Affinity of Homologated Adenosine Analogues as ABulletin of the Korean Chemical SocietyArticle
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Abstract
The highly selective agonists of the A(3) adenosine receptor (AR), Cl-IB-MECA (2-chloro-N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine), and its 4'-thio analogue, were successfully converted into selective antagonists simply by appending a second N-methyl group on the 5'-uronamide position. The 2-chloro-5'-(N,N-dimethyl)uronamido analogues bound to, but did not activate, the human A(3)AR, with K(i) values of 29 nM (4'-O) and 15 nM (4'-S), showing >100-fold selectivity over A(1), A(2A), and A(2B)ARs. Competitive antagonism was demonstrated by Schild analysis. The 2-(dimethylamino)-5'-(N,N-dimethyl)uronamido substitution also retained A(3)AR selectivity but lowered affinity.
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